


Standin' at the Crossroads

by Pimento, VenezuelanWriter



Category: Supernatural
Genre: 1930s, Alternate Universe - Prohibition Era, Alternate Universe- No Supernatural, Explicit Sexual Content, Family Drama, Flashbacks, M/M
Language: English
Status: Completed
Published: 2019-06-10
Updated: 2019-06-10
Packaged: 2020-03-08 08:13:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,471
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18890668
Author URL: https://archiveofourown.org/users/Pimento/pseuds/Pimento, https://archiveofourown.org/users/VenezuelanWriter/pseuds/VenezuelanWriter
Summary: So many things were out of place —starting with America. The economy was barely steading itself again, the Prohibition had people either going crazy or behind bars, and corruption knocked on everyone’s door at least once a day.Dean and Sam open up their own inn, trying to survive in the conflictive society, but one day a particular customer arrives and makes Dean question what side of the history he’s on.





	Standin' at the Crossroads

**Author's Note:**

> This is the first bang that I signed-up for and I’m so happy I did.
> 
> Working with pimentogirl (check her out on [tumblr](https://pimentogirl.tumblr.com/) and [AO3](https://archiveofourown.org/users/Pimento/pseuds/Pimento)), the talented artist of the pieces of this fic and also its beta reader, was a dream come true. She’s truly one of my favorite creators on this fandom. I hope we do it again sometime, Pimmy!
> 
> Find [here](https://archiveofourown.org/works/19153828) the masterpost with the art. Go give that some love, please!!
> 
> Title because of [Jonhson's song.](https://open.spotify.com/track/1TrGdXSgiBm8W68D2K1COG?autoplay=true&v=T)

 

 

_1933 - Present Day_

“We’re going to be so late,” Dean said, kissing Cas’ cheek before sliding his feet off the edge of the bed.

“Oh, but wasn’t it worth it,” Cas breathed out, a faded smile on his lips.

Dean turned around, eyeing the white stripes on Cas’ stomach. He shrugged.

“You’re right. There’s always time for sex.”

“And for catching the wets,” Cas said. He also slipped off the bed, sitting on the opposite side of it. “So... mind if I shower first?” he asked.

The silence before a reply was long, longer than usual, and Cas realized what he’d said.

Dean’s plain answer cut through the air.

“Sure, go ahead. I'll make breakfast.”

Cas sighed loudly.

“Yeah, you don’t like that I call them wets,” he said, turning to put a gentle hand on Dean’s bare shoulder blade.

“We’re fucking hypocrites, Cas,” Dean spat.

Cas took a quiet silent breath, standing up and walking to the bathroom.

“We’re making a living out of this, without going to jail. I think I’m okay with it.”

Dean put on his sleeping clothes —tee and boxers— and went to the kitchen.

He started preparing pancake mix, adding more flour than necessary and noticing too late that there weren’t enough eggs. Still, he poured a fair amount on the pan and waited for it to cook.

He wasn’t taking it out on the pancakes. He just couldn’t put more love into his cooking when he was, again, doubting his life choices.

He wondered if he’d do things differently if he could go back in time, to that day when Cas and he were only strangers and the last one when there weren’t secrets between he and Sam.

Dean returned to present day when the burning smell hit his nose. He grabbed the iron pan and took it off the stove, serving the ruined breakfast on a plate.

“All good?” Cas asked, walking out of their bedroom.

He was wearing his dress pants and white undershirt.

“You know that I miss Sam,” Dean rambled. “I miss the time when I was still taller than him and the economy in this country hadn’t gone to shit.”

He put the plate on his table spot and poured more mix in the pan.

“I know, Dean. I know it’s never been easy being apart.”

Cas walked to him. He’d shaven; Dean could tell because the jaw on the uncovered part of his shoulder was soft, even fresh.

“You know I haven’t talked to Gabriel since I was 15 and he was 18,” Cas continued. “I haven’t even seen him.” He pressed a chaste kiss near Dean’s neck, sending chills over his body.

“I know,” he whispered. He put a hand over Cas’, hugging his torso, and squeezed it tight.

“Could you please not burn my breakfast?” Cas asked playfully, gently untangling from Dean’s back.

Dean snorted.

“You got it, sunshine.”

⬧

_February 1927_

The lighting was dim in the Winchester’s basement, there was a brand-new record player in a corner, playing some Joseph Meyer’s song, and around ten men and a couple of women were gathered in the almost-empty room.

It was barely filled with a large dark table, that served as their bar, and some sets of couches for people to sit and enjoy their drinks and cigarettes.

Sam was serving a new customer a Manhattan drink, when there was a knock on the independent door of the basement. It was the coded knock: five taps, then two. It was for Sammy’s birthday, that they’d made it up.

Dean and Sam exchanged a look. They didn’t know the word was spreading so fast about the still-nameless-Inn.

“I’ll take it,” Dean said, walking to the metal door.

He opened the security grill, hinges squeaking as he did so.

On the other side of the grill, there was a pair of bright blue eyes.

“What’re you looking for, pal?” Dean asked.

“I heard this is the best place to buy salt.”

Dean nodded, closing the slit door and opening the person-sized one.

A man, probably around his own age, walked in the warm place.

His eyes weren’t the only pretty thing he had: his features were rough and manly, he was wearing one of the most expensive suits Dean had ever seen, with a black scarf around his neck and a fucking fedora hat that elegantly tied up his style.

The man looked around, finally giving Dean a kind look and walking to the table where Sam was.

“Evening, gentlemen,” he said. Dean, although he’d already heard the man’s voice over the door, suddenly realized how raspy it was. “What do you have?”

“Uh-”

“What do you want?” Dean interrupted Sam, walking to stand next to him on the opposite side of the table.

He leaned on it, arching his eyebrows and tilting his head in a flirtatious motion. His sixth sense was never wrong about this kinda thing.

“Give me a Stinger,” the man said, sitting on a wooden stool.

“Want a smoke?” Dean asked, while serving him the brandy.

“I don’t smoke, but thank you.”

Dean thought his brother and him were the only ones that didn’t do it. The thing was a freaking trend, but they didn’t like the bitter taste and the feeling of burning smoke getting in their lungs without ever being able to get it out.

As Dean put the drink in front of the man on the table, making hard eye contact with him, Sam luckily noticed he was being extra and pretended there was something interesting to see on the opposite side of the room.

Dean bent and reached for another stool under the table and sat in front of the man.

“How did you hear about us?”

The man took off his hat, putting it on the table. His hair was messy, dark, and contrasted amazingly with the color of his eyes.

He took a sip from the glass and shrugged.

“I’m someone of good contacts, what can I say.”

Dean licked his lips, accepting the challenge of getting this man’s attention.

Not much later, he’d learned that his name was Castiel, and he was just reckless enough to reveal his own real name, too.

“Is there somewhere more private where we can go?” Castiel asked after his third drink, staring at Dean’s torso then back at his eyes.

“I can’t leave my brother alone if there are clients. If you wait long enough, though, they’ll leave eventually.”

Castiel —Cas, from then on— nodded, looking at the couple of customers left in the basement.

“I think it’ll be worth the wait.”

⬧

_Present day_

Dean had to admit his love for cars wasn’t something recent. From the moment he laid eyes on Ford’s Model A, he knew there was a whole passion behind it.

That’s why he spoiled his Darling so much, a jet black cabriolet Phaeton of the year, with her strong boxy front and soft flowing curves making her sexy as fuck.

“It’s still three blocks away, right?” Dean asked behind the wheel, smoothly hitting the brakes at a stop sign.

“Yeah,” Cas said. “What a beautiful dog.”

Dean turned around. Beyond Cas’ fedora and fine profile, there was fancy woman walking a Saint Bernard on the street. She wore a dark purple silk puff sleeved, belted waist and exaggerated yokes. The dog, though, counteracted her elegance and finesse by dumping on the sidewalk.

“Indeed,” Dean agreed dryly.

They’d always wanted a dog, but it never seemed like the right time for it between keeping their cover, and their jobs, and their amenities intact.

“By the way,” Dean said, hitting the pedal again, “when is Crowley paying us for The Paradise Club?”

“I talked to him on the blower a few days ago. He said he’s still pushing the press, the owner is playing the bruno.”

Dean nodded. He felt uncomfortable in his own skin knowing the kind of thing “pushing the press” might imply, but he didn’t comment on it.

They fell into silence, the strain of Beiderbecke’s cornet crackling over the expensive radio, that Dean had insisted on despite it costing a third as much as the whole car, the only thing defying the tension.  

“I don’t know what’s so great about making music a competition,” Dean said, changing the station. “I wonder when they’ll do something other than jazz and fucking swing”.

“Who knows,” Cas said. “This is much better, though.” He turned up the volume of the soap opera and Dean rolled his eyes.

“Wow, I’m in love with a 50-year-old lady,” he joked. “You sure we shouldn’t get you half a dozen cats instead of a dog?”

Cas huffed a laugh.

“I don’t think that was your opinion earlier this morning.” Dean was gonna argue back, but Cas didn’t let him. “Now hush, I wanna know what happens next.”

⬧

_November 1927_

After they’d closed the inn, Dean finally confronted his brother. And, as expected, it didn’t go well.

They weren’t talking long, Sam standing in front of the table-slash-bar, and Dean sweeping the floor round the couches nearer the entrance before Sam exploded.

“Dean!” he exclaimed, before sighing tiredly and crossed his arms to lean on the table. “There’s no way you can convince me about this. We’ve been running this place, risking our asses for months, we’re just starting to turn a profit,” he shrugged, “and now you wanna throw it all away?”

“Well, at least we could stop hiding all the time! Is living on the line really fun for you?”

“That man you’re so stuck on sure has gotten in your head, huh.”

Sam hung his arms to his sides again, and walked to the opposite side of the table to grab his cloth. There was still some cleaning to do.

But Dean wasn’t going to let him cut off the discussion.

“Cas. His name is Cas. Castiel, to you, in fact,” he corrected. He walked to Sam, trying to calm down. “And he could’ve dropped the dime on us, so be thankful he didn’t.”

“How do you know he won’t?” Sam turned to face him again. “Fuck, maybe he’s just the palooka for some high pillow fat cat, waiting until we’re making enough Kale to take his graft.”

“He’s not, there’s not,” Dean said, so serene and so convinced it irritated Sam even further. “He promised, alright?”

“Oh, and you believe him?”

“Yes, Sam! Of course, I believe him, I love him, all right! And I can tell he’s not lying about this. He would never do anything to harm either of us. Dammit, can’t you just listen?”

“I’ve listened enough! Man, he really does have you dancing to his tune, don’t he. I’m not gonna quit it, okay? Even less so, just for the sake of being a turncoat.”.

Dean nodded slowly, taking a deep breath. “Well, I am.”

No, Dean was not serious about it.

“Then forget you ever knew me,” Sam dared him.

But the concern on Dean’s face actually got Sam. Dean _was_ serious about it.

“Wait, no, Sam, we’re brothers.”

The rage only hit Sam harder.

“Brothers are loyal to each other!”

If he could only see the bigger picture, Dean thought. “It’s a wise decision, Sammy.”

“Don’t Sammy me, alright?” His voice was raspy hurt. “Just go and move in with your daisy, Dean. And don’t think it’s a swing door, I want nothing to do with you if you’re gonna quit.”

Dean felt his eyes watering, but he couldn’t care less about his tears. Had his brother just cut him dead? The insult to Cas made the dismissal all the harder to take. Just like that? After everything they’d gone through together? “Didn’t have you down as a blue nose, Sam.”

Dean turned around and walked to the exit, stunned. Was this really happening?

He was almost at the metallic door, ready to leave and maybe never return, when he turned around one last time.

“If I ever change my mind?”

Sam looked up from a drink he’d just served himself.

“Huh?”

“If I ever change my mind, will we be good again?”

“You’d have to earn my trust back.”

Dean nodded. His chest stung with the anticipation of grief —because just about the only thing  his father had taught him was how to grieve people who were still alive.

“Okay.”

⬧

_Present day_

The cover was an office building. What a classic.

As soon as they opened the elevator door on the last floor, two suited men blocked their way out.

“Poughkeepsie,” Castiel blurted out.

Immediately, two things happened: the men nodded and let them in, and Dean’s blood ran cold.

He’d never told Cas about how he and Sam had made that one their word for emergencies, in case one of them got caught by the cops.

He regretted not having asked Cas more details about the place before they got there.

They walked into the main ‘office’, Cas completely oblivious to Dean’s fear.

The first thing Dean noticed was the actual bar at the bottom. It was way more elaborate than any they’d seen before, and with a wide variety of bottles on show, too.

The second thing, well, it was _a_ thing. Behind the bar and the bottles, there was a mirror with the name of the place: it read in thick, elongated letters _Tall Sam’s Saloon_.

If the codeword had raised his suspicions, this was the hammer blow.

“Uh, Cas,” Dean whispered, following Cas to the bar. “We have to go.”

He looked around, recognizing the height, hair, shoulder and back of his brother.

“Now,” he hissed urgently.

“What’s wrong?” But Cas saw for himself what the problem was.

Sam turned around, spotting Dean and Cas. His expression went from blank to distant panic.

“It’ll be too suspicious if we just go like this, Dean,” Cas whispered back.

They’d made it to the bar by then, within easy earshot of the younger Winchester, standing tall and cold behind his bar.

“Gentlemen,” Sam greeted. Setting the empty glass in his hand upside down on a line of similar glasses, his other hand reaching under the counter of the dark wooden furniture. Better safe than sorry. “I advise you to vamoose, before things get _awkward.”_ He let the clunk of metal on wood and the gentle click of the hammer explain just what awkward might entail.

“Fuck, Sam,” Dean hissed. Six years without seeing each other, even wondering if he may be dead or in jail, and that’s what he got? “We’re calling this off. No snitching.” Sam’s eyebrows raised. “Did Cas or I go after you when I left, Sammy?”

His brother had a point, but Dean had betrayed him once for Cas and Sam could only assume that, over the years, his loyalty to Castiel had just gotten stronger.

“Leave, Dean.”

“Or what? You’ll shoot me?”

“Someone could.” Sam pointed with his chin to the men in front of the elevator door.

Dean’s mouth hung open. Not dramatically or anything. But there was a distinct gap between his lips because he was actually speechless.

He collected his thoughts as Cas put a hand on his upper back, keeping him grounded.

“Sam,” he took a deep breath, staring into his eyes, “I know you distrust me. I get it, okay? But you’re my brother and if this isn’t some sort of destiny shit telling me that we never should’ve stopped talking, then I don’t know what it is.”

Sam sighed. He put the gun away.

⬧

_August 1927_

Dean never doubted that he was gay, but God he wondered if he could get any gayer than he was.

Being on all fours on Cas’ bed, legs spread, with Cas’ tongue lapping his asshole… wow, _that_ was what he called gay. And he was more than okay with it.

“Fuck, fuck, fuck, Cas-” he moaned, arching his back and pushing back against Cas.

“You really like that, huh?”

Dean put a forearm full on the bed and reached with his other hand for his dick.

Castiel smiled.

“I got you,” he murmured against Dean’s asscheek, biting it softly, to trail his way back to Dean’s hole with wet kisses and wrapped a hand around Dean.

It felt so good having Cas like that, burying his face deep in his ass —it was so fucking intimate.

His eyes shut tight as Cas’ hand did all the right things, at all the right moments, and _holy shit that tongue-fucking_ —

Dean blissed out with a strangled moan escaping his lips. Cas continued to kiss his exposed hole, the slick flesh around it, his lower back... He put his hands on each of Dean’s hips, so he’d know he was done. Dean collapsed on his back and Cas climbed on top of him, hard-on rubbing deliciously against Dean’s thigh.

Dean’s arms travelled up Cas’ sides, amazed by how perfect the man was.

Cas’ thumb caressed Dean’s cheek. He leaned in for a kiss; a slow one, sweet, gentle. Like the lovers they were.

Dean scratched Cas’ naked ass, slapping it softly and barely audible.

“Mm,” Cas moaned, and Dean did it again, harder this time.

Dean was pleased to know Cas was enjoying himself, and decided to give him something every sane men on the Earth loved: head.

He held Cas by his ribs twisting and dropping him onto his back.

Cas didn’t need to question Dean’s plan. He encouraged him in advance, petting his hair and leading him to his cock.

“God, you’re gorgeous,” Cas panted.

Dean blushed, starting to suck Cas off with ease and practiced skill, relaxing his jaw and tensing his lips. Moaning when he sensed Cas swelling, to encourage him to fuck his mouth as much as he wanted, pressing his tongue firm to the base of his cock as he climaxed and swallowing everything afterwards.

Cas dragged Dean into his arms when he flopped down next to him, cuddling him and kissing the top of his head. They were sweaty, but it was the least of their concerns. The closeness and the stickiness was anything but uncomfortable when the only thing they could think about was holding each other.

“Dean?”

“Yeah?” Dean answered, with a sleepy voice. It was late, and it’d been a long day.

“You should shut your gin joint. Come work with me.”

Dean’s brain felt like it was actually turning itself back on.

“What?”

“Yeah, baby. Sam could, too. Crowley told me he didn’t mind me bringing in more people, so long as they were loyal.”

Dean put weight on his side and looked down at Cas.

“He doesn’t know how we met, huh?”

Cas frowned. “Of course not. I told him you were a customer in another place and he believes your and Sam’s last venture was a failed job.”

Dean felt curious.

“What did you tell him, that the place burned down or something?”

Cas’ eyes focused on the ceiling.

“That it wasn’t a speakeasy in the first place.”

Dean stared at Cas long enough to make Cas look at him again.

“He trusts you.”

“And I trust you. Evidently, yeah, but, I mean…” Cas’ eyes went to his toes. It was complicated. “This is so risky. He’d kill me if he knew.”

Dean nodded, feeling his heart squeeze at the mere thought. He returned to snuggle deeper into Cas’ chest. “I know.”

Cas tapped his arm and he looked up. Cas was smiling almost nostalgically. They kissed slowly, mostly smooching. Kiss, snuggle, soft giggle, repeat.

Eventually, with how tired he was, Dean gave up and rested fully on his side, ready to sleep.

“So?” Cas asked with a low voice, scared Dean was already asleep.

“I’ll think about it and talk to Sam, alright?” Dean mumbled, closed-eyed.

Cas smiled to himself, kissing Dean’s forehead before drifting off to sleep.

⬧

_Present day_

“So,” Sam said, leaning over the bar, “Are you drinking or not?”

Dean finally felt some air getting to his lungs. He pulled his wallet out and grabbed a bill. “Give us-”

“Yeah, one on the rocks and a Stinger,” Sam said. He slid the bill back to Dean. “It’s on the house.”

Dean smiled, relieved and satisfied.

He turned to Cas. Cas offered him a grin, sharing his happiness with him.

Sam served them their drinks, grabbing a beer for himself.

_“To us.”_

_“To never being apart again.”_

_“To making the right decision for once.”_

They toasted in silence, sipping from their drinks with the gentle twang of a blues guitar playing the devil’s music in the background.

Yeah, Dean was working for some blackmailing bastard and he had a lot of work to do in his relationship with his brother, but he wasn’t alone in this and maybe, after all, standin’ at the crossroads wouldn’t be the death of him.

 

**Author's Note:**

> I hope you’ve enjoyed this, as much as I enjoyed the process (trust me, I did some research) of writing it.
> 
> Find me on tumblr: [@marian-elisa](https://marian-elisa.tumblr.com/) ♥.


End file.
